m-Chloroperbenzoic acid → 6-Bromoisoquinolin-1(2H)-one

Participants

Reaction Steps

A solution of Intermediate 94 (1.04 g) in methylene chloride (3 ml) was added with a solution of 3-chloroperbenzoic acid (2.16 g) in methylene chloride (3 ml), and stirred for 20 hours. The reaction mixture was added with methylene chloride (200 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. A solution of the residue in acetic anhydride (10 ml) was refluxed by heating for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was added with 2.5 N aqueous sodium hydroxide (20 ml), and stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature, and neutralized with 5 N aqueous hydrochloric acid under ice cooling to obtain the precipitated title compound (Intermediate 95, 623 mg).

Provenance & Evidence